Furan → 1-(Furan-2-yl)-2-(3-benzyloxyphenyl)ethan-1-one

HRID 1803629Notes

Reaction equation

HRID 1803629 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:15][C:16]([OH:18])=O)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:19]1[CH:23]=[CH:22][CH:21]=[CH:20]1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl>[O:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[C:16](=[O:18])[CH2:15][C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:10]=1

Participants

5

Reactant 3

HCID 8029FuranHCID 9845Trifluoroacetic anhydrideHCID 4592030(3-Benzyloxyphenyl)acetic acid

Product 1

HCID 711700351-(Furan-2-yl)-2-(3-benzyloxyphenyl)ethan-1-oneYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Benzyloxyphenylacetic acid (3.5 kg, 14.45 mol) was dissolved in CH2Cl2 (35 L), and furan (3.0 kg, 44 mol) and trifluoroacetic anhydride (4.55 kg, 21.65 mol) were added to the solution. The reaction was kept being stirred at room temperature for 2 days. The reaction was quenched with saturated NaHCO3 to pH=6.9, and the organic reagent in the mixture was evaporated. The residue was extracted with EtOAc, and the organic layer was washed with brine, dried over MgSO4, and evaporated. The resulting residue was purified by chromatography on a silica gel column using hexane-EtOAc as eluent to give the 1-(furan-2-yl)-2-(3-benzyloxyphenyl)ethan-1-one as yellow oil: 4 kg (yield: 95%)

Workup

  1. customThe reaction was quenched with saturated NaHCO3 to pH=6.9
  2. customthe organic reagent in the mixture was evaporated
  3. extractionThe residue was extracted with EtOAc
  4. washthe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customThe resulting residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-2ae8e23ad425433eb5add05167ade981
Source dataset
uspto-grants-2013_01
Patent number
US08350090B1

Reaction notes

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